Hey, guys. I’ve been wanting to write a blackmail Cuckold story for such a long time and I’m so glad I’ve finally finished this one, I’ve loved writing it every step of the way.

As always, I appreciate and enjoy the comments you post, they help me grow as a writer and it’s just good fun (plus plenty of you have very Hot ideas for potential sequels) so please share away and let me know what you think, and if you’d like this story to continue to what may lay beyond or if you think it’s a good ending point.

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Business was booming. Tim rolled up to the office in his new Audi, stepped out in his expensive tailored suit, and walked into his pride and joy: his business.

Tim had always been an entrepreneur, even from a young age. He was always finding ways to make money. Some of his methods had been dubious at best and as he grew older, they only became more dubious. He wasn’t afraid to crush the little man or resort to dirty tactics to get ahead, and it had made him a very rich man indeed.

For about half of last year, things had been dire. Tim blamed a number of things for his business’ sharp decline. It was a rocky time, but that’s where Tim flourished. He was adept in the dark arts of business, and he needed to flex those muscles to get the business out of this bind.

It wasn’t pretty, there were harsh redundancies, people bullied out of roles, and a large share of illegal practices and dodgy dealings. But for Tim, these were necessary evils to maintain his profit margin and his actions returned his business to prosperity and he was back on top. And of course, Tim thought he’d covered his tracks extremely well.

The first crack appeared when Ben, the IT guy, knocked on Tim’s door. If Ben hadn’t been both cheap and indispensable to the running of the company, Tim would’ve fired him a long time ago. The scrawny pale stereotypical early 20-somethings nerd walked into his office meekly. He had acne and terrible teeth, bulky glasses, and an ill-fitting cheap suit. He just didn’t fit the mould Tim envisioned, but he was an absolute wizard and Tim needed that level of expertise.

“What is it?” Tim said, already frustrated by his existence.

“Good morning, sir.” Ben said, he’d always had this creepy confidence to him, despite his appearance. The women in the office felt extremely uncomfortable when he was around.

“I’m busy, Ben.”

“I know, sir, but I’ve found something that needs your attention.” Ben placed a folder on the table and opened it for Tim to read. It was printouts of some reports and some spreadsheets. Tim immediately clocked them as areas where he’d conducted a lot of illegitimate activities and froze. “I noticed these anomalies when I was checking something out.” He added.

“It’s nothing, don’t worry about it.” Tim replied quickly.

“But sir, if you look here–“

“Who do you think you are? Do what you’re told. You’re overstepping completely. I’ll sort it. Just forget about it, Ben. Get back to your department and do your job.” Tim snapped, losing his cool. He closed the folder of paperwork and placed it in the bin next to him.

Ben looked at him with a controlled and cool gaze, reading him. “I’m sorry, sir. I’ll go back now and ‘do my job’, sir.” He said, pivoting on his heels and walking out. Tim rubbed his temples in frustration, he had a mess to fix now, one that would take all day.

And it did. By six o’clock, Tim had recovered his tracks completely and all traces of his misdeeds were once again buried. Relieved, he locked up for the night and headed home.

Home was a genuinely nice, large house in a nice community. It was the sort of community where everyone had a gate and none of the wives worked. Tim was no exception and he walked into an embrace from his housewife, Emma.

“Welcome home, sweetheart.” She said, planting a kiss on his cheek. Now in her early 40s, Emma was still quite the looker. Sure, she’d put on a little weight, but her figure was still amazing, and she carried it well, more curvy than overweight. Most of the weight had gone to her already massive breasts or padded her huge Ass. No matter how conservatively she dressed, she was never able to conceal those most erotic features, the wide hips and tight waist didn’t help as it merely accentuated her features. She was pretty too, with a soft and innocent homely face and long blonde hair.

The two sat down for dinner and conversation, then curled up on the sofa to watch some terrible film together. The two got along famously, always had done. They’d started dating when they were barely teenagers and stayed together through everything. They were now happily married for just over 20 years and loved their life together.

They retired upstairs to bed where they made Love. Their Sex always had been vanilla but mutually satisfying and enjoyable. Emma had always been a bit shy around Sex, refusing to even sleep with Tim until they’d married. Tim had slowly opened her to new things, like blowjobs and she’d even let him give her head after some convincing, something she now thoroughly enjoyed. It was a good, stable, happy marriage and they both thought that nothing could change that.

A few days later, without knocking, Ben strolled into Tim’s office. He had another folder, this time much thicker, and his slimy confidence was radiating across the room. Tim was not impressed.

“Don’t just walk in here, knock first.”

“Oh, but sir, this time it’s too important to wait.” Ben smirked, placing the new folder on the table. “I know you told me to keep my nose out, but I couldn’t help it…I found a lot more. I know you tried to cover your tracks, but I made backups before you could work anymore magic.” Ben was dripping with confidence. Tim could feel himself going red with anger.

“I don’t know what you’re talking about, Ben.” He was practically shaking. Ben opened the folder and casually pointed a few elements. The pages were highlighted and circled in various places, with explanatory text and references that Tim didn’t understand. There was a running tally along the side, culminating in the number 32.

“Oh, don’t play silly with me, Tim. You’re a clever guy, this was really masterful. Really illegal but really masterful, I’m impressed. I had to get some buddies online to help me out, but we figured it out.” Ben was grinning like the Cheshire cat. “That big 32? That’s the jail time for all of this. You’ve been a bad boy, Tim. And I feel it’s my moral obligation as an upstanding citizen to report this to the relevant authorities.” Ben feigned an apologetic look, shaking his head.

“You wouldn’t, you’d be out of a job, the whole company would be gone.” Tim was seething, the more he looked the more he knew how screwed he was. His mouth was going dry. “What do you really want?” He said, narrowing his eyes.

“I’m shocked, you’re trying to bribe me? I suppose I shouldn’t be surprised with your,” Ben swept his hand theatrically over the folder in front of him, “History.” He rubbed his chin. “But I suppose I could be bought. Let’s talk about my salary again, Tim, and hope the conversation ends differently this time.”

The last salary review ended with Tim giving Ben a big 0% increase, it wasn’t much of a discussion at all with Tim shutting down anything Ben tried to say. Caught off balance, Tim cleared his throat, “I’d be prepared to offer you a 10% increase in your curr–“

Ben scoffed, cutting Tim off. “No, no that won’t do. That was very generous under most circumstances, Tim, but I’ve got you by the balls, let’s be frank.” Tim was furious, blood boiling beneath his skin. No one had talked to him with this level of disrespect, perhaps in his whole life or at least not since he was a child. “You’re doubling my salary. The business is doing very well, we can afford it, you’ll just need to drop your embezzling a smidge too.” Ben said.

“Double?! Are you fucking joking me?” Tim stood up in a rage, reaching across the table and grabbing Ben by the tie, pulling him closer. “Do you take me for some kind of pushover? I’ll break your fucking nose and fire you right now.” He was practically face-to-face with the ugly young man, with his acne and glasses. He expected Ben to be afraid, but he hadn’t lost that sickening smirk.

“Come now, Tim, I thought you were an intelligent man. 32 years. You’ll be rapidly approaching your eighties when they let you out. A withered old man. This is all I ask for. We both win this way. You stay Free, I get rich. It’s a win-win.” Tim let go and shoved him back, where Ben adjusted his tie and shirt.

“Fuck you.” Tim spat, furious, heart pounding.

“Well. I expected this to go better. I recommend you change your mind. You know where to find me and I suggest you do before the end of the day or I’ll do the right thing, believe me I will. Have a lovely day, sir.” Ben flashed an exaggerated smile before walking out to leave Tim alone again.

Tim immediately swiped his lamp off his desk, smashing it on the floor. Pacing the room, he undid his tie because air was refusing to enter his lungs. His universe was spiralling now, threatening to crash into the Earth spectacularly and catastrophically. He sat in his chair, head in hands, pulling at his thinning hair. This was a disaster.

By around half four, Tim had spent the entirety of the day fluctuating between rage and terror. The idea of prison horrified Tim, deeply. He refused to let Ben become aware of this, but it was one of his greatest fears. He couldn’t imagine anything more mind-numbing yet dangerous. He couldn’t go to prison, no matter what.

A few minutes later, he was entering the IT department. A large, messy room utilised now only by Ben after all the redundancies. It was a chaotic room covered in various components and hardware, half-dissected towers littering the surroundings. And it stunk of body odour too. Tim hated this room. And yet here he was, without a fair choice in the matter.

“So, Tim. Have you considered my generous offer?” Ben said, turning in his chair.

Tim grit his teeth. It took a lot for him to concede. “Yes.”

Ben slapped his knees, “Brilliant. We have a deal. My silence for your money. I promise I won’t ask for anything else.” Ben stood up from his chair and extended a hand for Tim to shake. Tim looked down at the hand like it was leprous. Ben held it there in the air, waiting.

“If you ask for anything else…I’ll kill you.” Tim said coldly. Ben just chortled, lowering his hand.

“Sure thing, Tim. I guess it’s either go to prison for a long time or you could do that and be there for the rest of your life. Or we can avoid all that nasty business.” Ben shrugged, going back to his desk. “See you tomorrow, sir.”

The drive home was white knuckled as Tim’s hands wrung the steering wheel as if it were Ben’s neck. There was liberal usage of his horn and some reckless abandon in his driving. He just wanted to get home.

He walked in, dropping his briefcase, and shrugging his coat off. He heard Emma call him upstairs. Curious, he made his way up to her. The bathroom door was open and inside Emma was running a bath. She’d lit candles and was burning some incense with soft music playing in the background. She stood up and hugged Tim, kissing him gently on the lips.

“Good evening, handsome. I’ve run you a bath, I thought you could use some pampering.” She said sweetly, holding him.

“You’re the best. You really are. You have no idea.” Tim was on the verge of tears. He stripped off and climbed in, letting the warm water soak him and relieve his stress. Emma followed suit, with Tim watching her disrobe. He loved her body, especially her giant breasts which still had some perkiness to them, topped with her large nipples. She climbed in the tub behind him and began to wash his back, massaging him.

Tim always told Emma everything. She already knew about the illicit activities at work, but she was horrified to find out about Ben’s blackmail. She leaned forward and kissed his cheek, rubbing his chest. “Oh darling, I’m so sorry. This is terrible. But we’ll get through it. We always have done.” She reassured.

“I Love you so much. We will. As long as you’re by my side I’ll be fine.”

“I’ll always be yours. And I’ll do anything to support you, darling.”

The two dried off and Tim picked his Wife up, her thick thighs wrapping around him, and carried her to the bed. The couple enjoyed an hour of passionate and loving missionary Sex, with Tim Cumming hard and deep inside his Wife. The two collapsed and held each other.

“Do you think it’s too late for us to have a child?” Emma asked quietly. “We’ve been trying for so long…”

He stroked her head, “No, sweetheart. I’m sure we’ll end up with a beautiful baby one day.” They snuggled up and fell asleep in each other’s arms. Tim felt at peace, soothed by a misplaced sense of security.

Tim braced for impact at work after the weekend, wondering how Ben was going to act. But he had no interactions with him. And the day after, the one time they interacted, Ben was respectful and deferential again. Monday, Tuesday, Wednesday, Thursday, it was all calm and back to normal. Tim was still uneasy but settling more now.

Friday rolled around and at lunch time there was a knock at his door. Calling them in, Tim was pleased to see it was Emma, looking beautiful in a long yellow summer dress with her hair up and carrying two bags. “Hey, handsome.” She said, walking in. “I know this week has been tough, so I thought I’d surprise you with lunch.” She beamed.

Tim’s face was pure appreciation. He pulled up another chair for his Wife and the two shared a delightful lunch together, chatting and laughing. It was exactly what Tim needed and he was looking forward to the weekend.

As Emma was getting ready to leave, there was another knock. Tim summoned the person in, and Ben oozed into the room. He immediately locked wide eyes on Emma, gaze lingering for just too long to be comfortable. “Sorry, sir. I didn’t realise you had company.” Ben said.

“This is my Wife, Emma. We were just having lunch, she’s just about to leave.” Tim said coolly. He could sense Emma’s discomfort.

“That’s a shame. I must say you look beautiful today, Emma, Tim is a very lucky man.” Ben said, still looking at her.

“Thank you…I’ll go now, Tim. Thank you for lunch.” She pecked her husband on the cheek with her painted, thick red lips and quickly made an exit. Despite her modest dress showing no cleavage, it was impossible for Emma to hide her large 36G breasts, a fact Ben was enjoying immensely.

After she left, Ben looked back to Tim. “Wow, you really are lucky. I can only hope to be just as lucky one day.” He said, grinning.

“What do you want?” Tim said sharply.

“You know what, boss, I’ve forgotten. I’ll get back to you.” Ben said, turning and heading straight out. Tim felt a deep sense of unease after he left, like something bad was going to happen.

And it did, just as Tim was packing up to leave. Ben, once again, invited himself into Tim’s office and paced around. Tim froze up immediately, waiting for the storm. “What is it, Ben?” Tim said.

“Oh, I’ve been thinking and, look I really hate to do this but, I need to change our little arrangement. Just a little bit. You get how business works, Tim.”

Tim gripped his desk. “How much more?” He said plainly.

“Nah, it’s not money, Tim.” Ben walked around the office more and sat in the chair Emma had at lunch, swinging his legs up onto the desk. “You know, I can’t remember the last time I had my dick sucked. I’m sure that’s not a problem you have, you know, being a happily married man with a just beautiful Wife.” Ben looked at Tim with the smuggest look on his face.

Tim wasn’t connecting the dots; the implication wasn’t something that he could muster in his imagination.

“Now before I state plainly what’s going to happen, check your email.” Tim followed the instruction and saw an urgent email sitting in his inbox. Opening it revealed a list of emails: news reporters, police, anti-fraud. Below the list were pages and pages of what could be surmised as evidence of Tim’s illegal activities. It was a whole case, and it just went on and on, stating statutes and laws. Tim lost all colour in his face.

“It’s airtight, I’ve got backups of everything, all precautions have been taken…and that email sends tonight at 11:59, unless I stop it.” Ben leaned back, borderline chuckling at his own machinations. “Now, back to me and my needs. I have one last favour I need from you, Tim, then I’ll delete everything, I promise.”

Tim looked at him, sweating. “What is it?” He practically hissed.

“It’s quite simple and it won’t cost you a penny. OK so, I want to come over tomorrow and I want your pretty Wife to suck my cock.” Ben stated it as if he was asking to borrow sugar.

Tim erupted, rising out of his chair, and slamming Ben in the face with his fist, knocking the scrawny boy out of the chair and onto the ground. Tim stood over him, fists clenched at his side, breathing heavily.

Ben looked up at him from the ground, a little daze but still far too cocky for his own good, black eye already forming. “That’s fine, that’s fine…” He scampered on all fours towards the door before struggling to stand up, a little dizzy. “You can say no. Just remember what it means, Tim.” Ben spat a little blood on the floor. “Make sure you let me know by midnight otherwise say goodbye to your life.” He slammed the door behind him, leaving Tim alone and furious.

He repeatedly slammed his fists into the table, if he’d ever been close to a heart attack now was the time. He was fucked. Well and truly fucked. He stayed there for an hour, just wallowing, before returning home to face the music.

Emma could tell something was wrong instantly, she always could. She led Tim through into the kitchen where dinner was ready and poured him a stiff drink, which lasted all of two seconds after entering Tim’s reach. “Darling, what’s happened? Was it…him again?” She asked sympathetically.

Tim nodded.

“How much more did he want?” She said.

“It’s not money this time.” Tim said bitterly.

“What is it now, darling? It’ll be OK.” She tried to reassure him.

“He wants…” He looked up at his Wife, his beautiful and immensely innocent Wife, her pale skin, and kind blue eyes. The thought of her pleasuring any other man was unbearable…and the thought of it being that scrawny cunt Ben urged him to vomit. “…he wants you to give him a Blowjob.” He threw the now empty glass across the room, shattering it.

Emma gasped at the demand and the action, covering her face with her hands. “What? That’s…that’s disgusting, Tim. Oh my God.”

Tim took her in his arms, holding her. She sobbed gently. “It’s OK…I’ll tell him no. I’ve had some advice, it’ll be more likely 20 years. It’s my fault, I won’t let him drag you into this.” He said, rubbing her back and holding her tightly.

They ate dinner in near silence, with Emma sniffing occasionally. They sat and watched a film in the same way. Each minute passing dragging them closer to the deadline. At around 11, Emma reached over and held Tim’s hand. They looked at each other and Emma said: “I’ll do it.”

Tim looked at her, shaking his head. “Sweetheart, no. You can’t. I can’t let him disrespect you that way.”

“What I can’t do is be without you for that long, Tim. I Love you and I need you. I’ll do it, I’ll do what he asks.” She said, defeated, squeezing her husband’s hand.

Tim sat, grinding his teeth. This was the most humiliation he’d ever felt. It was downright obscene. He hated Ben with every fibre of his body…but he was terrified beneath the bluster. Petrified of the consequences of his actions, of being locked away and separated from his Wife, losing any chance of raising a family with her.

“OK…I’ll tell him.” The two hugged, both sobbing. The lowest point to date for both Tim and Emma, but unfortunately not to be their rock bottom.